Facile route to air and moisture stable β-difluoroboryl acrylamides

A method for the preparation of air stable difluoroboryl acrylamides is reported. In contrast to the ubiquitous organotrifluoroborate salts, difluoroboryl acrylamides are relatively nonpolar and are readily purified by silica gel chromatography. Difluoroboryl acrylamides serve as efficient substrates in cross-coupling reactions to afford the corresponding trisubstituted acrylamides in good to excellent yields. The utility of the difluoroboryl group in various chemical transformations is presented.

Name thesis:degree_name

M.S.

Level thesis:degree_level

masters

Discipline thesis:degree_discipline

Organic Chemistry

Department dc:contributor.department

Chemistry

Grantor dc:publisher

Virginia Tech

Year dc:date.issued

2019

Author dc:creator

• Medici, Eric

Chair dc:contributor.committeechair

• Santos, Webster L.

Committee members dc:contributor.committeemember

• Carlier, Paul R.
• Matson, John B.
• Tanko, James M.

• difluoroboryl acrylamide
• difluoroborane
• fluorination
• cross-coupling
• Oxidation

Statement dc:rights

• Creative Commons Attribution 4.0 International

Licence dc:rights.uri

• http://creativecommons.org/licenses/by/4.0/

Language dc:language.iso

en_US

Handle dc:identifier.uri

http://hdl.handle.net/10919/95059

OAI identifier oai:identifier

oai:vtechworks.lib.vt.edu:10919/95059